NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	270.225
LogP:	2.192
LogD:	2.089
LogS:	-2.935
# Rotatable Bonds:	5
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	2.969
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.541
MDCK Permeability:	3.7577905459329486e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	56.141517639160156%
Volume Distribution (VD):	0.795
Pgp-substrate:	64.14373016357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.712
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	7.334
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.959
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.315
Skin Sensitization:	0.499
Carcinogencity:	0.86
Eye Corrosion:	0.677
Eye Irritation:	0.538
Respiratory Toxicity:	0.943

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC66246

Natural Product ID:	NPC66246
*Common Name:**	12-Acetyloxy-Tremetone
IUPAC Name:	2-[(2S)-5-acetyl-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl acetate
Synonyms:	12-Acetyloxy-Tremetone
Standard InCHIKey:	CMOGDVKTFYEQGC-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-9(8-18-11(3)17)15-7-13-6-12(10(2)16)4-5-14(13)19-15/h4-6,15H,1,7-8H2,2-3H3/t15-/m0/s1
SMILES:	C=C(COC(=O)C)[C@@H]1Cc2cc(ccc2O1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223939
PubChem CID:	23900103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32653	helichrysum italicum ssp. microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315926]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	75.0	%	PMID[463217]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	9.8	day	PMID[463217]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC66246 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	1505
0.2-0.3	3745
0.3-0.4	8780
0.4-0.5	9699
0.5-0.6	4221
0.6-0.7	8464
0.7-0.8	5483
0.8-0.85	457
0.85-0.9	22
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC170546
0.9919	High Similarity	NPC282230
0.9919	High Similarity	NPC183348
0.9839	High Similarity	NPC196979
0.9839	High Similarity	NPC470977
0.9839	High Similarity	NPC15083
0.9839	High Similarity	NPC470976
0.9512	High Similarity	NPC470858
0.9508	High Similarity	NPC141252
0.9508	High Similarity	NPC11799
0.9213	High Similarity	NPC939
0.9104	High Similarity	NPC470856
0.9	High Similarity	NPC470859
0.8906	High Similarity	NPC293387
0.8864	High Similarity	NPC247743
0.876	High Similarity	NPC37512
0.875	High Similarity	NPC165556
0.8699	High Similarity	NPC470860
0.8692	High Similarity	NPC50583
0.8676	High Similarity	NPC36414
0.8643	High Similarity	NPC286038
0.8636	High Similarity	NPC279596
0.8626	High Similarity	NPC473019
0.8603	High Similarity	NPC253616
0.8582	High Similarity	NPC66991
0.8561	High Similarity	NPC109778
0.856	High Similarity	NPC293424
0.8551	High Similarity	NPC184053
0.8538	High Similarity	NPC237868
0.8529	High Similarity	NPC268081
0.8507	High Similarity	NPC55147
0.85	High Similarity	NPC213900
0.8489	Intermediate Similarity	NPC171870
0.8478	Intermediate Similarity	NPC137009
0.8478	Intermediate Similarity	NPC472515
0.8478	Intermediate Similarity	NPC37206
0.8473	Intermediate Similarity	NPC121104
0.8443	Intermediate Similarity	NPC23332
0.844	Intermediate Similarity	NPC171656
0.844	Intermediate Similarity	NPC208584
0.8425	Intermediate Similarity	NPC230951
0.8421	Intermediate Similarity	NPC327457
0.8421	Intermediate Similarity	NPC86774
0.8409	Intermediate Similarity	NPC473744
0.8409	Intermediate Similarity	NPC2401
0.8406	Intermediate Similarity	NPC473988
0.8403	Intermediate Similarity	NPC191104
0.8394	Intermediate Similarity	NPC472516
0.8387	Intermediate Similarity	NPC252004
0.8385	Intermediate Similarity	NPC221798
0.8385	Intermediate Similarity	NPC89630
0.8385	Intermediate Similarity	NPC184219
0.8382	Intermediate Similarity	NPC470844
0.8372	Intermediate Similarity	NPC69403
0.8372	Intermediate Similarity	NPC291189
0.837	Intermediate Similarity	NPC229646
0.837	Intermediate Similarity	NPC54503
0.8369	Intermediate Similarity	NPC184702
0.8361	Intermediate Similarity	NPC183648
0.8357	Intermediate Similarity	NPC254010
0.8345	Intermediate Similarity	NPC136095
0.8345	Intermediate Similarity	NPC11566
0.8345	Intermediate Similarity	NPC262635
0.8333	Intermediate Similarity	NPC217423
0.8333	Intermediate Similarity	NPC45104
0.8333	Intermediate Similarity	NPC104172
0.8333	Intermediate Similarity	NPC259685
0.8333	Intermediate Similarity	NPC88445
0.8333	Intermediate Similarity	NPC469954
0.8333	Intermediate Similarity	NPC88886
0.8322	Intermediate Similarity	NPC14875
0.8322	Intermediate Similarity	NPC74539
0.8322	Intermediate Similarity	NPC304443
0.832	Intermediate Similarity	NPC220540
0.831	Intermediate Similarity	NPC294365
0.8309	Intermediate Similarity	NPC209858
0.8298	Intermediate Similarity	NPC51146
0.8298	Intermediate Similarity	NPC313036
0.8298	Intermediate Similarity	NPC166858
0.8296	Intermediate Similarity	NPC175159
0.8286	Intermediate Similarity	NPC307990
0.8286	Intermediate Similarity	NPC16455
0.8264	Intermediate Similarity	NPC266743
0.8264	Intermediate Similarity	NPC168085
0.8261	Intermediate Similarity	NPC29638
0.8261	Intermediate Similarity	NPC254741
0.8258	Intermediate Similarity	NPC475236
0.8258	Intermediate Similarity	NPC234109
0.8258	Intermediate Similarity	NPC474737
0.8258	Intermediate Similarity	NPC188327
0.8252	Intermediate Similarity	NPC471346
0.8248	Intermediate Similarity	NPC229128
0.8243	Intermediate Similarity	NPC470625
0.8235	Intermediate Similarity	NPC7526
0.8235	Intermediate Similarity	NPC66158
0.8235	Intermediate Similarity	NPC222036
0.8231	Intermediate Similarity	NPC131725
0.8231	Intermediate Similarity	NPC67300
0.8227	Intermediate Similarity	NPC297985
0.8227	Intermediate Similarity	NPC229916
0.8222	Intermediate Similarity	NPC472517
0.8222	Intermediate Similarity	NPC473777
0.8222	Intermediate Similarity	NPC125153
0.8219	Intermediate Similarity	NPC290671
0.8214	Intermediate Similarity	NPC473209
0.8211	Intermediate Similarity	NPC473809
0.8207	Intermediate Similarity	NPC317492
0.8207	Intermediate Similarity	NPC164299
0.8201	Intermediate Similarity	NPC38153
0.8201	Intermediate Similarity	NPC62735
0.8201	Intermediate Similarity	NPC103001
0.8194	Intermediate Similarity	NPC471285
0.8188	Intermediate Similarity	NPC46869
0.8188	Intermediate Similarity	NPC283331
0.8188	Intermediate Similarity	NPC99854
0.8188	Intermediate Similarity	NPC269495
0.8188	Intermediate Similarity	NPC163029
0.8182	Intermediate Similarity	NPC474044
0.8182	Intermediate Similarity	NPC65041
0.8182	Intermediate Similarity	NPC316535
0.8182	Intermediate Similarity	NPC470857
0.8182	Intermediate Similarity	NPC246903
0.8175	Intermediate Similarity	NPC55149
0.8175	Intermediate Similarity	NPC311339
0.8175	Intermediate Similarity	NPC188907
0.8175	Intermediate Similarity	NPC307412
0.8169	Intermediate Similarity	NPC130206
0.8169	Intermediate Similarity	NPC471639
0.8169	Intermediate Similarity	NPC472344
0.8169	Intermediate Similarity	NPC147145
0.8169	Intermediate Similarity	NPC471643
0.8163	Intermediate Similarity	NPC10429
0.8162	Intermediate Similarity	NPC302844
0.8162	Intermediate Similarity	NPC14248
0.8156	Intermediate Similarity	NPC472409
0.8154	Intermediate Similarity	NPC314329
0.8151	Intermediate Similarity	NPC180351
0.8151	Intermediate Similarity	NPC472421
0.8148	Intermediate Similarity	NPC245395
0.8145	Intermediate Similarity	NPC57879
0.8138	Intermediate Similarity	NPC95526
0.8134	Intermediate Similarity	NPC2596
0.8134	Intermediate Similarity	NPC125887
0.8134	Intermediate Similarity	NPC473907
0.813	Intermediate Similarity	NPC259554
0.8129	Intermediate Similarity	NPC156910
0.8129	Intermediate Similarity	NPC161196
0.8125	Intermediate Similarity	NPC206007
0.8125	Intermediate Similarity	NPC190572
0.8116	Intermediate Similarity	NPC217914
0.8116	Intermediate Similarity	NPC125269
0.8116	Intermediate Similarity	NPC61499
0.8116	Intermediate Similarity	NPC164136
0.8112	Intermediate Similarity	NPC257097
0.8112	Intermediate Similarity	NPC221432
0.8112	Intermediate Similarity	NPC59522
0.8112	Intermediate Similarity	NPC175504
0.8112	Intermediate Similarity	NPC150408
0.8112	Intermediate Similarity	NPC143896
0.8112	Intermediate Similarity	NPC310130
0.8112	Intermediate Similarity	NPC164980
0.8112	Intermediate Similarity	NPC149026
0.8112	Intermediate Similarity	NPC91560
0.8112	Intermediate Similarity	NPC68104
0.8112	Intermediate Similarity	NPC39329
0.8112	Intermediate Similarity	NPC470932
0.8112	Intermediate Similarity	NPC75049
0.8112	Intermediate Similarity	NPC290038
0.8112	Intermediate Similarity	NPC17262
0.8112	Intermediate Similarity	NPC169591
0.8106	Intermediate Similarity	NPC107846
0.8102	Intermediate Similarity	NPC287533
0.8099	Intermediate Similarity	NPC27220
0.8099	Intermediate Similarity	NPC471640
0.8099	Intermediate Similarity	NPC22467
0.8099	Intermediate Similarity	NPC201820
0.8099	Intermediate Similarity	NPC471644
0.8095	Intermediate Similarity	NPC98028
0.8095	Intermediate Similarity	NPC472423
0.8095	Intermediate Similarity	NPC474744
0.8095	Intermediate Similarity	NPC318424
0.8095	Intermediate Similarity	NPC474772
0.8095	Intermediate Similarity	NPC472580
0.8092	Intermediate Similarity	NPC311219
0.8085	Intermediate Similarity	NPC23257
0.8085	Intermediate Similarity	NPC139554
0.8082	Intermediate Similarity	NPC39929
0.8082	Intermediate Similarity	NPC472298
0.8082	Intermediate Similarity	NPC296030
0.808	Intermediate Similarity	NPC199462
0.8079	Intermediate Similarity	NPC74749
0.8079	Intermediate Similarity	NPC43971
0.8079	Intermediate Similarity	NPC19554
0.8079	Intermediate Similarity	NPC49009
0.8074	Intermediate Similarity	NPC238309
0.8074	Intermediate Similarity	NPC168710
0.8074	Intermediate Similarity	NPC473894
0.8071	Intermediate Similarity	NPC332594
0.8071	Intermediate Similarity	NPC233707
0.8069	Intermediate Similarity	NPC218300

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC66246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	963
0.2-0.3	1503
0.3-0.4	2457
0.4-0.5	1973
0.5-0.6	1240
0.6-0.7	546
0.7-0.8	188
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1243	Approved
0.8322	Intermediate Similarity	NPD920	Approved
0.8321	Intermediate Similarity	NPD2799	Discontinued
0.8306	Intermediate Similarity	NPD1241	Discontinued
0.8298	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD6832	Phase 2
0.8261	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1019	Discontinued
0.8108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD9717	Approved
0.8071	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4628	Phase 3
0.8015	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7986	Intermediate Similarity	NPD6799	Approved
0.7973	Intermediate Similarity	NPD7411	Suspended
0.7972	Intermediate Similarity	NPD3887	Approved
0.7955	Intermediate Similarity	NPD3972	Approved
0.7947	Intermediate Similarity	NPD7075	Discontinued
0.7929	Intermediate Similarity	NPD3748	Approved
0.7923	Intermediate Similarity	NPD5691	Approved
0.7919	Intermediate Similarity	NPD6801	Discontinued
0.791	Intermediate Similarity	NPD3266	Approved
0.791	Intermediate Similarity	NPD3267	Approved
0.7899	Intermediate Similarity	NPD4307	Phase 2
0.7895	Intermediate Similarity	NPD919	Approved
0.7887	Intermediate Similarity	NPD1549	Phase 2
0.7883	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD9545	Approved
0.7842	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6355	Discontinued
0.7823	Intermediate Similarity	NPD1358	Approved
0.7817	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2344	Approved
0.7808	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD1203	Approved
0.777	Intermediate Similarity	NPD3142	Approved
0.777	Intermediate Similarity	NPD3140	Approved
0.7754	Intermediate Similarity	NPD6798	Discontinued
0.7754	Intermediate Similarity	NPD3268	Approved
0.7742	Intermediate Similarity	NPD6808	Phase 2
0.7742	Intermediate Similarity	NPD3134	Approved
0.7727	Intermediate Similarity	NPD17	Approved
0.7727	Intermediate Similarity	NPD5494	Approved
0.7718	Intermediate Similarity	NPD7458	Discontinued
0.7704	Intermediate Similarity	NPD1876	Approved
0.7692	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1471	Phase 3
0.7692	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2353	Approved
0.7692	Intermediate Similarity	NPD6004	Phase 3
0.7692	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6002	Phase 3
0.7692	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD6005	Phase 3
0.7687	Intermediate Similarity	NPD2534	Approved
0.7687	Intermediate Similarity	NPD2532	Approved
0.7687	Intermediate Similarity	NPD2533	Approved
0.7676	Intermediate Similarity	NPD4308	Phase 3
0.7676	Intermediate Similarity	NPD1510	Phase 2
0.7658	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD2797	Approved
0.7643	Intermediate Similarity	NPD1240	Approved
0.7638	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6273	Approved
0.7632	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD411	Approved
0.7622	Intermediate Similarity	NPD4476	Approved
0.7622	Intermediate Similarity	NPD4477	Approved
0.7612	Intermediate Similarity	NPD1281	Approved
0.7603	Intermediate Similarity	NPD2309	Approved
0.76	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4626	Approved
0.7594	Intermediate Similarity	NPD1778	Approved
0.7591	Intermediate Similarity	NPD2798	Approved
0.7589	Intermediate Similarity	NPD447	Suspended
0.7589	Intermediate Similarity	NPD1933	Approved
0.7584	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD1608	Approved
0.7552	Intermediate Similarity	NPD7033	Discontinued
0.755	Intermediate Similarity	NPD4380	Phase 2
0.7537	Intermediate Similarity	NPD3496	Discontinued
0.7535	Intermediate Similarity	NPD1607	Approved
0.7534	Intermediate Similarity	NPD7003	Approved
0.7532	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD9697	Approved
0.7519	Intermediate Similarity	NPD5535	Approved
0.7519	Intermediate Similarity	NPD1651	Approved
0.7518	Intermediate Similarity	NPD2979	Phase 3
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5049	Phase 3
0.7517	Intermediate Similarity	NPD2424	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD5889	Approved
0.7483	Intermediate Similarity	NPD2354	Approved
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7466	Intermediate Similarity	NPD2800	Approved
0.7452	Intermediate Similarity	NPD1247	Approved
0.7451	Intermediate Similarity	NPD6279	Approved
0.7451	Intermediate Similarity	NPD6280	Approved
0.7447	Intermediate Similarity	NPD8032	Phase 2
0.7447	Intermediate Similarity	NPD6233	Phase 2
0.7445	Intermediate Similarity	NPD1283	Approved
0.7444	Intermediate Similarity	NPD1894	Discontinued
0.7419	Intermediate Similarity	NPD3882	Suspended
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7351	Intermediate Similarity	NPD5403	Approved
0.7347	Intermediate Similarity	NPD2654	Approved
0.7338	Intermediate Similarity	NPD1934	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5401	Approved
0.7324	Intermediate Similarity	NPD4062	Phase 3
0.732	Intermediate Similarity	NPD6585	Discontinued
0.7303	Intermediate Similarity	NPD957	Approved
0.7301	Intermediate Similarity	NPD5953	Discontinued
0.7299	Intermediate Similarity	NPD1481	Phase 2
0.7297	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD9494	Approved
0.7285	Intermediate Similarity	NPD2186	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2531	Phase 2
0.7259	Intermediate Similarity	NPD5585	Approved
0.7259	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6559	Discontinued
0.7254	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD1535	Discovery
0.7226	Intermediate Similarity	NPD1611	Approved
0.7226	Intermediate Similarity	NPD422	Phase 1
0.7222	Intermediate Similarity	NPD4622	Approved
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7222	Intermediate Similarity	NPD9261	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7222	Intermediate Similarity	NPD4618	Approved
0.7214	Intermediate Similarity	NPD5647	Approved
0.7209	Intermediate Similarity	NPD2684	Approved
0.7209	Intermediate Similarity	NPD2182	Approved
0.72	Intermediate Similarity	NPD7440	Discontinued
0.7194	Intermediate Similarity	NPD3225	Approved
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4110	Phase 3
0.7178	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7286	Phase 2
0.7163	Intermediate Similarity	NPD454	Approved
0.7162	Intermediate Similarity	NPD2897	Discontinued
0.7161	Intermediate Similarity	NPD958	Approved
0.7153	Intermediate Similarity	NPD3847	Discontinued
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD6362	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7134	Intermediate Similarity	NPD5402	Approved
0.7132	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD290	Approved
0.7125	Intermediate Similarity	NPD6959	Discontinued
0.7124	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5688	Approved
0.7123	Intermediate Similarity	NPD5689	Approved
0.7123	Intermediate Similarity	NPD7097	Phase 1
0.7121	Intermediate Similarity	NPD7843	Approved
0.712	Intermediate Similarity	NPD1238	Approved
0.7113	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2614	Approved
0.7111	Intermediate Similarity	NPD5536	Phase 2
0.7105	Intermediate Similarity	NPD4662	Approved
0.7105	Intermediate Similarity	NPD4661	Approved
0.709	Intermediate Similarity	NPD7157	Approved
0.7081	Intermediate Similarity	NPD7229	Phase 3
0.708	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD2801	Approved
0.7059	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD6653	Approved
0.7055	Intermediate Similarity	NPD6651	Approved
0.7051	Intermediate Similarity	NPD6385	Approved
0.7051	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6386	Approved
0.7047	Intermediate Similarity	NPD5958	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data